Chatham Homes for Sale

Welcome to Chatham, Massachusetts—a picturesque coastal gem nestled in the heart of Cape Cod. Known for its charming New England vibe, Chatham offers a unique blend of stunning natural beauty, rich history, and a vibrant community atmosphere. With its captivating beaches, scenic harbors, and quaint downtown, this idyllic town is a haven for families, retirees, and anyone seeking a tranquil escape by the sea.

Chatham boasts an array of outdoor activities, from sailing and fishing in the Atlantic Ocean to hiking the beautiful trails of the Monomoy National Wildlife Refuge. The town’s historic lighthouse, iconic windmill, and charming shops and restaurants add to its allure, making it a perfect destination for both residents and visitors alike.

For those considering a move to this enchanting area, the current homes for sale in Chatham offer an exciting opportunity to embrace the coastal lifestyle. From classic Cape Cod cottages to luxurious waterfront properties, there’s something to suit every taste and budget. Many homes feature breathtaking views, spacious yards, and easy access to the town’s beautiful beaches and vibrant community events.

Whether you’re looking for a year-round residence or a summer retreat, Chatham’s real estate market is brimming with possibilities. With its friendly atmosphere, strong sense of community, and endless recreational opportunities, Chatham is not just a place to live—it's a lifestyle. Explore the homes for sale in this charming town and discover the perfect setting for your next chapter!

Newest Chatham Homes for Sale

$12,000,000

4 Beds ⋅ 3 Baths ⋅ 22603612 MLS

The SandBox, an icon of Shore Road, sits on one of the most coveted streets in America, steps from the Chatham Bars Inn - where waterfront estates are generational and cherished. Set on an over one-acre lot with immense beachfront, the home reflects the architectural heritage of the setting, with classic cedar shake and shingle detailing throughout. A staircase framed by flowering landscaping leads to a bluestone patio and entertaining spaces over the beach, with a private trail to the water's edge -- one of the first points on the Eastern Seaboard to greet the sunrise each morning. Inside, a shiplap-clad great room opens the home for gathering, flowing into dining and kitchen areas with water views from every angle. The primary suite is a private retreat framed by its own bay window, while well-appointed guest spaces offer comfort for family and friends. Extensively renovated, the home retains the craftsmanship of its original build - true, enduring Cape Cod character. This is where summers are made. Shore Road beachfront grows more coveted with time, and opportunities like this rarely surface - a chance to secure one of the most aspirational addresses on the entire East Coast.

166 Shore Road, Chatham

$950,000

3 Beds ⋅ 1 Baths ⋅ 22603601 MLS

This charming cottage is in a coveted location close to Hardings Beach and Barn HIll town Landing with iconic oyster shanties and access to Oyster River, Stage Harbor for kayaking & paddleboarding. 2 marinas are also nearby for boating fun not to mention all the local dining options and bike trail. This adorable quintessential Cape Cod cottage has been updated with newer kitchen and bath, skylights, decorated with panache enhancing summer rental investment. Detached 2 car garage is a bonus and the unique '' sleeping under the stars'' porch in the trees adds to the ambiance, creating memorable happy summers in Chatham. Connected to town sewer on a level 23, 741 sq ft lot, it offers many possibilities for potential expansion. Furnace non functional, buyer to install new one or mini splits for heat/AC if desired. Opportunity Knocks! Showings ONLY on Sunday rental turnover days July 26th, Aug 2nd, Aug.16th only 12-3PM.

268 Barn Hill Road, Chatham

$695,000

2 Beds ⋅ 1 Baths ⋅ 22603438 MLS

Nestled on a private lane in one of Chatham's most sought after locations, this home has been enjoyed by the same family since 1946 and occupied as a year round home for 40 years. This is a rare opportunity to create your own Cape Cod retreat just moments from Oyster River, the Oyster River Boatyard, and nearby Hardings Beach. Bring your vision to the charming, light-filled home full of original character, vaulted ceilings and ready for its next chapter. Whether you're dreaming of restoring its vintage charm or exploring future possibilities, this is a rare chance to own in Chatham. The property is being sold AS IS. Buyers should anticipate the need for a new Title V septic system and replacement of the existing oil tank to meet current town requirements. All information contained herein is deemed reliable but is not guaranteed. Buyers & buyers agents should perform their own due diligence regarding future use and development potential and independently verify all information.

40 Uncle Abner's Path, Chatham

$9,995,000

3 Beds ⋅ 3 Baths ⋅ 22603522 MLS

Shore Road is more than an address. It's a feeling. The moment you turn onto it, the mood quietly shifts. Clipped hedges, impossibly pretty gardens, sparkling water views, and the grand Chatham Bars Inn create a storybook setting. Offered for the first time in almost four decades, ''Offshore'' encompasses more than an acre on Shore Road - an exceptional combination of land, privacy, and possibility. Beyond the home's welcoming presence, a surprisingly private landscape unfolds, where mature plantings, a sweeping lawn, a carriage-style garage, and a swimming pool create an extraordinary retreat. Inside, the home was designed for gracious living, with spacious rooms and classic details, equally suited to entertaining or savoring a quiet afternoon. Views of Chatham Harbor, North Beach, and the Atlantic provide a lovely backdrop from the main living areas, while upstairs, charming windows frame picture-perfect coastal scenes. Whether enjoyed as it is today or reimagined, this is a rare opportunity to begin its next chapter. This special property invites its next owner to create a lasting legacy along one of Chatham's most iconic streets.

153 Shore Road, Chatham

$795,000

4 Beds ⋅ 4 Baths ⋅ 22603514 MLS

Tucked away on a cul-de-sac in W. Chatham this spacious 4 bed/ 3.5 bath Cape offers potential in a peaceful setting. Set back from the road with a canopy of trees, this property feels private & serene with seasonal views of a scenic cranberry bog & birdlife. The main level features an open sunny living/dining area, 2 picture windows & slider to wraparound deck, hardwood floors and wood burning Fireplace. The good sized kitchen has wet bar and Breakfast bar seating, Stack WD laundry& pantry area, plus half bath in hallway. The 1st Fl primary bedroom is ensuite with bath. Upstairs are 3 good sized bedrooms, full bath & ample storage closet. The 674 sq ft finished walk out lower level with separate entrance slider offers flexibility for office, TV entertainment room with built in bar ready for gatherings. Nearby is the CC Rail Trail access for biking/ walking or Marion's Pie shop for coffee, a short drive to Ridgevale Beach. Excellent opportunity for next owner to bring their vision and updates to make it truly shine. Great for year round or vacation rental options...lots of possibilities with 3 levels of living space.

19 Joshuas Way, Chatham

$4,250,000

3 Beds ⋅ 4 Baths ⋅ 22603504 MLS

Exceptional waterfront estate offering breathtaking views from nearly every room and a private sandy beach. Lovingly owned by the same family for nearly three decades, this spectacular 3 bedroom, 3.5 bath residence offers three levels of beautifully designed living overlooking Crow's Pond. A grand foyer opens to a dramatic living room with soaring ceilings, a fireplace, walls of windows, and sweeping water views. Glass doors lead from the living room to a deck and patio overlooking the water, creating the perfect setting for entertaining or relaxing. The first floor also features a waterfront dining room, kitchen, spacious primary suite, wood-paneled den, powder room, laundry, and an attached two-car garage. A charming side porch provides yet another inviting outdoor retreat with spectacular water views. Upstairs, two guest bedrooms enjoy water views and share a full bath. The walkout lower level offers a family room, office, full bath, natural light, and excellent storage. Experience Cape Cod's finest waterfront living with boating, kayaking, swimming, and fishing right from your private sandy beach. Ideally located next to Eastward Ho! and a short drive to downtown Chatham.

600 Fox Hill Road, Chatham

$2,390,000

4 Beds ⋅ 4 Baths ⋅ 22603375 MLS

Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath. Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Possible subdivision opportunity.

55 Winterset Drive, Chatham

$1,469,000

5 Beds ⋅ 10 Baths ⋅ 22603353 MLS

New co-ownership opportunity: own one-eighth of this professionally managed, turnkey home by Pacaso. Fox Hill sits on 2.74 acres in Chatham, a renovated coastal estate with sweeping views of Crows Pond, Eastward Ho, and Pleasant Bay from nearly every angle. The classic shingle-style exterior includes a two-car garage and private boat dock with direct water access. The airy living room features a stone fireplace, window seats, and vast water views. The kitchen continues the view with a Wolf gas range, a large island, and doors opening to a deck overlooking Crows Pond. A formal dining room with raised panel walls and a butler's pantry with wet bar completes the main level. The three-level layout includes a quiet office, lower-level gym, indoor sauna, and a guest suite with its own kitchen and living room, all connected by an elevator. A pool, patio, and private dock anchor the outdoor spaces, with sunrise and sunset views from multiple balconies. Lighthouse Beach is close by, and Chatham's Main Street offers galleries, restaurants, and shops. Professionally managed by Pacaso and ready when owners arrive.

558 Fox Hill Road, Chatham

$5,900,000

4 Beds ⋅ 5 Baths ⋅ 22603274 MLS

Classic Cape Cod home on a one-acre lot on the nicest street in Chatham.... Nooks and crannies and additions in several directions in this very private location of North Chatham...Choice of 3 primary bedrooms with attached baths... Views over Chatham Harbor and beyond.......Beach and boating just an easy walk away. Or swim and relax in your own backyard in the recently retiled heated Gunite pool....House has been very well maintained by the current owner who has been here for over 36 years and completed a new roof, many new windows, new bedroom addition, newer family room addition and more......All information here has not been independently verified and buyer should do his/her own due diligence by checking with their attorney, and zoning and building rules and by laws, etc.. Assessment numbers subject to change with new Fiscal Year.

95 Cotchpinicut Road, Chatham

$2,995,000

4 Beds ⋅ 4 Baths ⋅ 22603172 MLS

Perfectly positioned to capture breathtaking sunsets over Bucks Creek, this meticulously updated 2,700-square-foot residence features 4 bedrooms and 3.5 bathrooms. Just a short distance from Nantucket Sound and Hardings Beach, this craftsman-renovated home offers a spacious open floor plan highlighted by vaulted, beamed ceilings and expansive windows that showcase ever-shifting views of the tidal marsh. Designed to host guests, the first floor includes a stunning professional-grade kitchen with an oversized quartz island that opens to an elegant dining area, two fireplaces, and two primary bedroom suites. The property is rounded out by a large wrap-around deck, two additional second-floor bedrooms, a one-car garage, and a full basement with heat and air conditioning. The house is .7 mi from Harding's Beach and 1.9 miles from downtown Chatham's shops and restaurants. Pull up a chair and savor Mother Nature's ever-changing show.

26 Hardings Beach Road, Chatham

$1,275,000

3 Beds ⋅ 2 Baths ⋅ 22603060 MLS

Sought after neighborhood of Riverbay. Light and bright home with incredible gardens and fabulous outdoor space. Three bedrooms 2 newly redone baths with livingroom, dinng room and primary suite all with sliders onto the deck with spiral stairway to back yard for super summer fun. Room for a pool! Lower level could be finished off-high ceilings and windows overlooking the back yard. Deeded rights to 2 ponds for kayaking, canoeing and fishing. Come take a look at this special property.

240 Riverview Drive, Chatham

$1,069,000

3 Beds ⋅ 3 Baths ⋅ 22602982 MLS

Sprawling and spacious, 65 Captain Kendrick Drive presents an exceptional opportunity to own a beautifully situated 3 br 3 bath home in one of Chatham's most peaceful settings. Seasonal views of the Monomoy River create a serene backdrop, inviting relaxing vibes and a true sense of coastal tranquility.Offering 1,754 sqft of main-level living, the home many features include an updated eat-in kitchen, large living room with fireplace, and a dining room that leads you towards two distinct, comfortable sitting areas that open to expansive decks with winter water views. 1632 sf of additional finished space in the walkout lower level add tremendous flexibility. Recent improvements include a new roof, new windows, kitchen renovations, and cooling systems. Generous living spaces, thoughtful updates, and a serene Chatham setting, make this home ready to be enjoyed for years to come.

65 Captain Kendrick Drive, Chatham

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.